Electrochemical 1,2-Migration Reactions Mediated by Vitamin B12 Derivatives

  • Yoshio Hisaeda


Electrolyses of an alkyl halide having two ester groups and one phenyl group on the β-carbon atom have been carried out under various conditions in the presence of a catalytic amount of the hydrophobic vitamin B12. The migration of the pheny group was observed under the conditions forming a radical intermediate. The ester-migrated product was detected under the conditions forming an anionic intermediate. This is the first successful example in selecting a migrating group by electrolysis potential. A novel vitamin B12 derivative, which has phenylalanine residues on the peripheral side chains, catalyzed effectively 1,2-migration of the carboxylic ester in 1-bromo-2,2-bis(ethoxycarbonyl)propane at −1.0 V vs. Ag/AgCl under irradiation conditions.


Radical Intermediate Alkyl Halide Migrate Group Carboxylic Ester Phenylalanine Residue 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Yoshio Hisaeda
    • 1
  1. 1.Department of Chemistry and Biochemistry, Graduate School of EngineeringKyushu UniversityHakozaki, Higashi-ku, FukuokaJapan

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